Stereospecific and Stereoselective Rhodium(I)‐Catalyzed Intramolecular [2+2+2] Cycloaddition of Allene‐Ene‐Ynes: Construction of Bicyclo[4.1.0]heptenes

Ohta, Yuu; Yasuda, Shigeo; Yokogawa, Yuka; Kurokawa, Kei; Mukai, Chisato

doi:10.1002/anie.201409155

Cited by 36 publications

(23 citation statements)

References 60 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[14] Our group has al ong-standing interest in Pd-catalyzed C À Cb ond-forming reactions from allene-substituted unsaturated compounds,such as enallenes, allenynes,and bisallenes. [16] However,t he presence of these three p systems provides ac hallenge concerning control of regioselectivity in the reaction. [16] However,t he presence of these three p systems provides ac hallenge concerning control of regioselectivity in the reaction.…”

mentioning

confidence: 99%

Efficient Palladium‐Catalyzed Aerobic Arylative Carbocyclization of Enallenynes

et al. 2018

View full text Add to dashboard Cite

Herein, we communicate a selective and efficient protocol for oxidative arylating carbocyclization of enallenynes using O 2 as the oxidant. The key to success for this aerobic transformation is the application of a specific electron transfer mediator (ETM), a bifunctional catalyst consisting of a metal‐macrocycle and quinone moieties. This catalyst significantly facilitates the reoxidation of Pd 0 to Pd II under atmospheric pressure of O 2 . Diverse functionalized enallenynes react with aryl boronic acids to afford the corresponding cyclic tetraenes in moderate to good yields.

show abstract

mentioning

confidence: 99%

Efficient Palladium‐Catalyzed Aerobic Arylative Carbocyclization of Enallenynes

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Insertion of the remaining π-component into the C-Rh bond followed by reductive elimination would then afford the three-membered ring products 97. 51) Treatment of 96 with [RhCl(CO) 2 ] 2 effected the intramolecular [2+2+2]-type ring-closing reaction to produce various tetracyclic derivatives 97 containing a cyclopropane ring. The substrates with acyclic alkenes could also be used resulting in the formation of the tricyclic derivatives.…”

Section: Stereospecific and Stereoselective Rh-catalyzed [2+2+2] Cyclmentioning

confidence: 99%

Creation of Novel Cyclization Methods Using <i>sp</i>-Hybridized Carbon Units and Syntheses of Bioactive Compounds

Mukai

2017

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

Some recent results on the development of new and reliable procedures for the construction of diverse ring systems based on the chemistry of sp-hybridized species, especially allene functionality, are described. This review includes: (i) synthesis of the multi-cyclic skeletons by combination of the π-component of allene with suitable other π-components such as alkyne, alkene, or additional allene under Rh-catalyzed conditions; (ii) synthesis of heterocycles as well as carbocycles by reaction of the sp-hybridized center of allene with some nucleophiles in an endo-mode manner; and (iii) total syntheses of natural products and related compounds from the sp-hybridized starting materials.

show abstract

“…3). 16 Furthermore, we have developed a regioselective and partially intermolecular [2 2 2] cycloaddition of allene alkynes with alkynes to provide polysubstituted benzene derivatives (eq. 4).…”

Section: Bmentioning

confidence: 99%

“…The reaction is initiated by the formation of the rhodabicyclic intermediate I. 12,13,16 There might be two possible pathways for the following insertion process of the external alkyne 39. One is insertion into the C sp2 Rh bond leading to the two intermediates V and V and the other is insertion into the C sp3 Rh bond resulting in formation of the two other intermediates III and III .…”

Section: 39mentioning

confidence: 99%